Diethyl diallylmalonate

Base Information

• Chemical Name: Diethyl diallylmalonate
• CAS No.: 3195-24-2
• Molecular Formula: C13H20O4
• Molecular Weight: 240.299
• Hs Code.: 2917190090
• European Community (EC) Number: 221-696-4
• NSC Number: 46842,30683
• DSSTox Substance ID: DTXSID00185785
• Nikkaji Number: J151.156D
• Wikidata: Q63409574
• Mol file: 3195-24-2.mol

Synonyms:diethyl diallylmalonate

Chemical Property of Diethyl diallylmalonate

Chemical Property:

• Vapor Pressure: 0.032mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Boiling Point: 243.499 °C at 760 mmHg
• Flash Point: 106.728 °C
• PSA: 52.60000
• Density: 0.999 g/cm³
• LogP: 2.25120
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, DMSO, Methanol
• Water Solubility.: Sparingly Soluble in water. (0.72 g/L) (25°C)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 240.13615911
• Heavy Atom Count: 17
• Complexity: 264

Purity/Quality:

99.9% ^*data from raw suppliers

Diethyl Diallylmalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(CC=C)(CC=C)C(=O)OCC
• Uses: Diethyl diallylmalonate is the starting material for enantioselective synthesis of carbocyclic nucleoside analogues. It is also used as Low catalyst loading in ring-closing metathesis reaction. Cationic nickel (with monodentate phosphoramidites and Wilke?s azaphospholene as ligands) catalyzed cycloisomerisation of diethyl diallylmalonate has been reported.

Technology Process of Diethyl diallylmalonate

There total 64 articles about Diethyl diallylmalonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

Allyl acetate (591-87-7) + diethyl malonate (105-53-3) → (2-propenyl)propanedioic acid diethyl ester (2049-80-1) + diallylmalonic acid diethyl ester (3195-24-2)

Guidance literature:

With C₃₃H₃₃N₂O₄PPd; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 15h; Reagent/catalyst; Schlenk technique; Inert atmosphere;

DOI:10.1007/s11172-014-0739-8

Reference yield: 87.0%

Phenyl-phosphonothioic acid S-allyl ester O-ethyl ester (74070-96-5) + diethyl malonate (105-53-3) → (2-propenyl)propanedioic acid diethyl ester (2049-80-1) + diallylmalonic acid diethyl ester (3195-24-2)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 80 ℃; for 0.666667h; Product distribution;

DOI:10.1021/jo00156a029

Reference yield: 84.0%

allyl methyl carbonate (35466-83-2) + diethyl malonate (105-53-3) → (2-propenyl)propanedioic acid diethyl ester (2049-80-1) + diallylmalonic acid diethyl ester (3195-24-2)

Guidance literature:

With triphenylphosphine; In water; at 50 ℃; for 24h;

DOI:10.1016/j.apcata.2010.08.010

upstream raw materials:

allyl iodid

sodium ethanolate

diethyl malonate

allyl bromide

Downstream raw materials:

3,8-bis-bromomethyl-2,7-dioxa-spiro[4.4]nonane-1,6-dione

3,8-bis-chloromethyl-2,7-dioxa-spiro[4.4]nonane-1,6-dione

3-allyl-5-methyl-2-oxo-tetrahydro-furan-3-carboxylic acid thiocarbamoylamide

5,5-Diallyl-2-thio-barbitursaeure

Refernces

• 1、 Brace, Neal O.. "Reactions of 2-(perfluoroalkyl)ethane thiols with 1,6-heptadiene and 4-substituted 1,6-heptadienes: The synthesis of RFethanethio- cyclopentanoic and -dioic acids; and, "geminal-twin-tail" bis-(perfluoroalkylethanethio)alkanoic acids". . p. 7 - 15. Retrieved 2005.
• 2、 Kim, Aihong,Hong, Joon. "Simple synthesis and anti-HIV activity of novel cyclopentene phosphonate nucleosides". . p. 1 - 8. Retrieved 2006.
• 3、 Van Ornum, Scott G.,Cook, James M.. "Generation of four five-membered rings in a one pot process. Studies directed toward the synthesis of dicyclopenta[a,d]pentalene via the tandem Pauson-Khand reaction". . p. 7185 - 7188. Retrieved 1996.
• 4、 Nikitas, Nikolaos F.,Voutyritsa, Errika,Gkizis, Petros L.,Kokotos, Christoforos G.. "Metal-free Photochemical Atom Transfer Radical Addition (ATRA) of BrCCl3 to Alkenes". supporting information. p. 96 - 101. Retrieved 2021/01/04.
• 5、 Escudero, Julien,Bellosta, Véronique,Cossy, Janine. "Rhodium-Catalyzed Cyclization of O,ω-Unsaturated Alkoxyamines: Formation of Oxygen-Containing Heterocycles". supporting information. p. 574 - 578. Retrieved 2018/02/21.